My way of dressing is pretty manly already. When I had short(er) hair, I looked like a guy from behind because of my back and shoulders. I enjoy dressing up that way, though. It's comfortable, relatively cheap and it makes me less prone to having severely unwanted attention from others. Men's jackets are the $#!/!

Ive done it thrice; once for a play as a kid; and once my late teens during school spirit week, plus a last time in college.
The first of the later involved three classmates and I dressing like an all girl's teen pop band and doing a little skit inside a food court.
The second time involved an event during school week, which involved a challenge during freshmen week; it asked for a gy who dress and get prettied up as a lady, and since i was the thinnest guy in my class, i got forced into it.
The actual owner of the dress was jealous that it looked better on me because i has a slender frame; guess thats why i gained more weight and muscle during my later college years.